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39 Houses

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Whitman Woods - A Berkshire Vacation

Hancock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$172

Golden Triangle in the Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$2,869

Responds fast! avg. 1 hour 31 minutes

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$122

UMIQUE Country Condo, 1BR 1 BA - NEW

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

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Price per night from

$261

Mountainside Getaway @ Jiminy Peak In the Berkshires

Hancock house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$567

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$431

Great rentals within 20 miles that match your search

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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Price per night from

$327

Iris Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$172

Horse Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

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Price per night from

$172

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$263

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

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Price per night from

$820

Modern Cozy Wooded Retreat

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$153

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

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$373

Berkshire Farmhouse Vacation

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

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$299

Gartner House, a charming home in Lenox

Lenox apartment

  • 4 bedrooms
  • 1 bathroom
  • sleeps 7

“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.

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$230

The Meadow House 4 bdrm 4 bath house

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

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Price per night from

$724

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$218

Heart of Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

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Price per night from

$345

The Bear Den

North Adams apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$339

Hudson Valley Berkshires Cottage

Spencertown house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$197

The Heart of Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$402

Quite stay in the country

Nassau house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$299

Close to attractions in the Berkshires

South Lee hotel apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$115

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Price per night from

$1,260

Charming Guest Suite

Old Chatham apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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Price per night from

$155

Private Country home near Berkshires

Cherry Plain house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$98

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$802

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$572

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

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Price per night from

$744

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$458

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$659

1880s Home with a Postcard View

Williamstown house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

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Price per night from

$195

Berkshire house w/ fireplace, A/C, WiFi & laundry

Plainfield house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

“Peaceful country home” Beautiful, welcoming home in a perfect location. Warm and inviting living room; bright, airy bedrooms.

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Price per night from

$234

North Getaway Cottage

Williamstown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$172

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

Holiday Inn Club Vacations Oak N' Spruce 2br suite Friday check-ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$70

Retreat in the Woods

Savoy house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$229

6BR Berkshire Bliss - 38 private acres - close to skiing and town

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15

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Price per night from

$795

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